


The Spice Of Play Time

by HPslashSPNLuver92



Category: Supernatural
Genre: Bottom Sam, Crossdressing Sam Winchester, Established Relationship, M/M, Porn With Plot, Porn with Feelings, Roleplay, Sexual Roleplay, Top Dean, Top Dean Winchester/Bottom Sam Winchester, new tags with every new addition
Language: English
Status: In-Progress
Published: 2018-10-25
Updated: 2018-10-27
Packaged: 2019-08-07 12:49:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 7,361
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16408823
Author URL: https://archiveofourown.org/users/HPslashSPNLuver92/pseuds/HPslashSPNLuver92
Summary: Things are going well - the world wasn't ending, people weren't dying left or right, monsters decided to behave. The Winchester brothers have it good - then Sam gets an idea... Dean is all on board, of course.Set in the Bunker during a non-canon peaceful period, where the BMOL never interfered, Mary is resurrected, and Rowena is a - if you could say - friend of the boys (you'll see in the future ;P). Not sure about anyone else - except for Castiel, he will be in it later :)This is my tentative venture into shameless smut, but I can't stop plots happening still in my stories. But I'll try to focus on the shmexy times. :P





	1. The Setup

**Author's Note:**

> Please, be gentle, I'm not usually one to write porny goodness (no real experience...). I hope you will enjoy it anyway, and if you want to read other scenarios, feel free to suggest it. I'm already working on other snippets.
> 
> This is only the introduction, but starting from the next chapter, this story is gonna be series of oneshots, loosely entwined by some plot that comes to my mind. Which is why I'll update the tags with every new chapter.
> 
> WARNING: Anything in here is CONSENSUAL between the participants, even if it doesn't seem like it. Any time something happens that they actually don't like, you'll know. But just in case for the future: BE WARNED!

The library of the bunker was silent save for the soft hum of the laptop on one of the tables. The light of the map room and one of the table lamps illuminated the hunched over form of Sam Winchester, a frown of concentration on his paler features. His Adam’s apple was bobbing up and down every once in a while, followed by a deep breath in and a shaky sigh out. Wider hazel-green eyes roamed over the screen, studying the text displayed on it slowly and meticulously.

That was the scene that greeted Dean after his lonely breakfast in the kitchen. The older brother sighed with a dissatisfied grimace - no way was he pouting - as he suspected the younger man already digging up another case for them. He kinda hoped that they could have some alone time together, since the dangers eased up in the country.

Steeling himself against the disappointing reality of the outside world, he walked over to his brother. He couldn’t make out what was on the screen, but he had a different urge emerging inside him.

He leaned down and wrapped his arms around Sam’s shoulders, humming at the feel of the other’s warmth seeping into him.

His momentary joy was rudely interrupted by a jolt under him as Sam would’ve practically headbutted him if Dean’s head hadn’t been on his shoulder. Dean frowned: was his brother that absorbed in the research he didn’t even hear his approach?

The next moment, however, cleared it up - somewhat: Sam instantly slammed the laptop closed, almost breaking it with the force of his movement.

Dean’s eyes widened in shock at the sudden reaction his search for affection caused. He could feel Sam trembling in his hold and heard the pulse rapidly and loudly throbbing into his ear. His palm, resting on Sam’s left collarbone, was vibrating from the strong, fast beats of the younger man’s heart. It was a long time ago since he witnessed his brother being jumpscared by something.

"H-Hey" Sam tried, his voice cautious and shaky as he began taking deep breaths. "Did you sleep well?"

Dean checked his brother over from the corner of his eyes. Was he really seeing a tint of green crawling onto his cheeks? At least, Sam gripped Dean’s wrist, letting his thumb stroke the skin, as usual. Dean leaned in and pressed a kiss onto Sam’s cheek then tightened his hold around his brother, hoping to calm him down. Sam let out a sigh and leaned back some more, his body relaxing mostly.

"M-hmm..." Dean replied, once he was sure Sam will survive the fright of his life. It was strange behavior and he was determined to find out what was going on, but he can enjoy this moment with his little brother, filling a hole in his heart, caused by the lack of opportunity to be together because of hunts piled up. "You?"

"Me, too" Sam leaned his head against Dean’s and the older man could just see his eyes slide shut and his thin lips twitch into a faint smile.

"Good" he pressed a kiss onto Sam’s neck this time, smiling when Sam leaned into it with the tiniest of satisfied squeaks. Dean parted his lips, letting them slide over the warm skin, pulling them away with a soft smack. No matter how many times they’re showing affection to each other, these were Dean’s personal favorites - which he would never admit, of course.

With a sigh, he settled back onto Sam’s shoulder.

"Case?" he asked, slapping himself inwardly for the petulance sneaking into his voice.

Sam froze stiff as the older brother pointed at the laptop. In turn, Dean froze stiff instantly worried.

"I-I..." Sam stuttered out, but his voice died away. That broken syllable was enough to instill the fear of God into Dean. _‘Please’_ Dean thought with a slight desperation, _‘tell me it’s not another secret...’_

 _ _"__ N-No..." the younger Winchester finally forced out. Dean frowned confused. Did he speak out loud? Or-

Oh, no _case!_

Reluctantly, Dean pulled away then swiftly pulled a chair out and sat next to Sam. When he gazed at his little brother, Sam had a flush covering the previous green tint in his cheeks and his eyes tried their damnedest to find any target except him. He reached out and grabbed the trembling, lithe fingers resting on the tabletop now, threading their fingers together. Sam’s eyes flitted onto the hands and his shoulders sagged the tiniest bit.

"You wanna fill me in or do I have to wheedle it outta there?" Dean asked, nodding at the computer. Sam glanced up, eyes filled with terror. "No more secrets" the older man reminded him as he leaned forward. His voice dipped down, making Sam flinch and lower his head guiltily. "We promised each other, remember?"

"I know" Sam spoke softly, sliding his free hand over Dean’s, gripping it tightly. "It’s nothing like that. Just... embarrassing..."

"Even after everything?" Dean asked with some incredulity. "We’ve been intimate for over a year now. What could be more embarrassing?" He would’ve used his usual lingo if not for the skittish behavior of his brother. Pressing buttons of discomfort could switch into shame, which would take them back quite a few steps - into the negative.

Sam swallowed while he tried to gather his courage. Dean stayed in his place, keeping his eyes on the younger man’s face for any sign to step in or intervene. At last, Sam decided to spill.

"That’s... kinda it" his voice shook, but he plowed on. A true Winchester stubbornness... "We’ve been together for more than a year and..." Sam glanced up briefly, his cheeks flushed even darker, then his gaze was averted once more. "I don’t want you to... get bored of me..."

Dean straightened out, feeling surprise fill him - and some indignation.

"Nonono" Sam suddenly burst out, his hold on Dean’s hand tightening. His hazel-green eyes, filled with terror and love, finally lifted to his brother’s emerald ones and stayed there. "I don’t mean you would cheat on me or... or break up with me because I’m not enough for you. You’ve proven your faithfulness to me countless times."

"Then what?" Dean asked, unable to stay quiet. Sam grimaced but soldiered on.

"I just... You’re so used to the adrenaline on hunts... And I don’t know if... you’d want that rush from... _us. _"__

Before instinct could take over and ruin everything, Dean let himself think about what he just heard. It’s amazing how he changed his attitude after he started a relationship with Sam. He had been more methodical, more strategic in everything - including his brother.

"Sammy" he started. His brother had a hopeful but wary expression on his face as Dean spoke. "What we have is amazing. I already have enough rush from hunting, nowadays a bit too much even, so being more mellow in private is wonderful and... relaxing."

"But" Sam inserted with a nervous chuckle "it’s pretty vanilla considering."

"And that’s not bad" Dean objected. "I like to spend time with you, even if it’s just in silence and in bed or watching TV or you reading and me dozing or whatever. So never think I would give that up for any adrenaline rush in our lives, okay?"

Sam nodded - then gave a shaky teasing smirk:

"You’re losing your masculine edge."

"Shut up" Dean rolled his eyes dutifully. "Make note ‘cause I’m never gonna admit to it again."

"I’ll pop open the champagne then" Sam snorted out but at least he relaxed even more.

"Back to the topic" Dean continued, turning serious. Sam’s eyes widened back, watching him with sudden fear. "If... you want to bring some spice" he shrugged "I’m on board. As long as you want it and okay with it. I know I’ve always been the adventurous out of the two of us, so anything that you feel comfortable with is okay with me. But we need to - as much as I hate to say it - ‘communicate’. We have to Dr. Phil this shit up, like every regular moron."

Sam laughed softly at that and fully let his muscles unwind - much to Dean’s relief. Even during the more relaxed moments of their conversation Sam was wound tighter than a clock.

"Okay" the younger man agreed with a nod, his eyes now filled with nothing but love and adoration. That look always made Dean grin goofily, proud that he managed to cheer the love of his life up. Dean pulled Sam closer, who slid his chair to accommodate them, and wrapped an arm around his shoulders. He leaned in and cupped the sharp jaw tenderly, fusing their lips together into a firm, loving kiss. Sam sighed when they pulled apart, resting his forehead against Dean’s for a moment.

"So" the younger man spoke once he sat upright. He slid the laptop closer, opening it up. Dean checked the screen and found text on it, white characters on dark grey background.

"Is that-?"

"A fanfic, yeah" Sam admitted with a blush. "I wasn’t... I usually ignore this stuff but... when I got to thinking about us, I... I satisfied my curiosity."

"About what?" Dean asked curiously, trying to read some of the text. It seemed like that... Wincest stuff. Even though it was still creepy, he couldn’t deny that he found it appealing nowadays. Just a tiny bit...

"Some... spice, as you put it" Sam shrugged, the flush on his face now spreading onto his neck. Dean could feel the nape of his brother’s neck heating up under his arm. "It’s... pretty mild, considering, but I got interested, so..."

"What did you have in mind?" Dean turned his attention onto his brother. He wished Sam would just get to the point sometimes, he was actually getting interested which is when he hated waiting.

"Umm..." Sam paused for one more second of hesitation, then with a deep breath he finally - _finally_ \- spat it out:

"Roleplay..."

Dean tilted his head confused, frowning as he tried to scoop out the information out of Sam’s stalling silences.

"Like the LARP thing?" he tried, but Sam’s grimace was answer enough.

"Not exactly" the younger Winchester bit his lower lip nervously. His hands released Dean and found each other, fingers playing as a background distraction. "It’s... for the bedroom."

For the bedroom?

...

_Ooh..._

"Ah" Dean felt like a lightbulb went off inside and above his head. "So porn live."

"Jeez" Sam exhaled, burying his even redder face into his palm. "You just _had to_  say that."

"Yup" Dean grinned. He was starting to like this idea already. "So what have you been reading? Some barbarian-sorceress action? Or pirate-on-pirate time?"

"Nothing _that_ cheesy" Sam grumbled with a roll of his eyes once he emerged. "Just dabbling in some... scenarios."

"So" Dean scooted closer, brushing his nose against Sam’s neck and jaw, before whispering into his ear "wanna try one out now?"

Sam visibly shivered, but his body leaned towards the stimulations, so Dean knew the younger man wasn’t opposed to the idea.

"Dean" his voice, however, showed some resistance. "We can’t just jump into this. We don’t even have a s-safeword."

Dean sighed in mock-annoyance, but he knew perfectly well that his brother was right. He pulled his head back but stayed close to Sam, showing he agreed with him. Sam smirked at him in a way that practically screamed that he was aware and that he thought his big brother was a horndog.

"What could be used as a safeword, anyway?" he asked, trying to coax Sam into this whole thing, hoping he would gradually get into it.

"Well, it has to be something... unrelated" Sam replied, frowning as he wracked his big brain. "Something that would snap us out of the scene if necessary."

"Yeah, we can get pretty into things, can we?" Dean mumbled, rubbing Sam’s shoulders absentmindedly. Sam hummed in agreement and they sank into their own inner vocabularies.

"Poughkeepsie, maybe?" Dean suggested a couple minutes later.

"No" Sam shook his head slowly as he thought it over. "It’s too connected to hunting. We should find something different, separate."

Another few minutes spent in silence...

"This is harder than I thought" Dean exclaimed, leaning back in his chair and scratching his head. Judging by the grimace slowly overtaking Sam’s face, the younger man was having just as much trouble. "It has to be something-"

"How about ‘District’?" Sam blurted out, cutting his brother’s complaints off.

"District?" Dean raised an eyebrow at the odd choice. "How did you come to that?"

"I was thinking something red like a stop sign or traffic light" Sam shrugged hesitantly. "Then my brain jumped to... brothels..." Dean felt himself grinning as another deep blush spread over Sam’s cheeks. He forgot how easily Sam was colored so pretty by just a few words... "You know, red light districts..."

"Isn’t that a little complicated?" Dean asked, keeping to the topic despite how much he wanted to kiss Sam stupid right now. "I mean it’s a bit of a big leap, isn’t it?"

"It’s different enough to snap us out" Sam said. "Once that happens we can associate. But it’s still something that could stop the scene quickly... don’t you think?"

"Yeah, you’re right there. It’s not like it could be used that much during sex."

The blunt ending of his sentence should’ve sent Sam onto the floor, unconscious from blood loss - or blood overflow, if the redness was anything to go by. Dean shifted back to his brother, wrapping his arms around his lean torso. Sam willingly tilted into his embrace, resting his head on Dean’s shoulder, hiding his flushed features.

"All right" Dean spoke, rubbing his brother’s back soothingly. "The most important thing is done." He lifted Sam’s head back up and nipped tenderly at the protruding cheekbone in front of him. He loved how the redness accentuated the fox-like features, getting him instantly in the mood.

He had one more important question, however.

"What do you want to roleplay first?"

_TBC_

**Notes for the Chapter:**

> Hope you liked the prologue! Next will be the first scene. Stay tuned!
> 
>  
> 
> ... And I suck at titles. -.-


	2. Private Lesson

**Summary for the Chapter:**

> Sam and Dean's first roleplay scene. Dean gets more than he expected - in a VERY positive way.
> 
> Crossdress!Sam inside!

**Notes for the Chapter:**

> Here's the first scene! It might be a bit cheesy, but let's start with something simple.
> 
> I don't know how frequently I'm gonna post other scenes, it will depend on inspiration and/or the suggestions from you guys. But I have a couple small plots planned during this, until those, though, I want to write some smaller scenes between the boys.
> 
> Enjoy!

Sam stared at the bags standing in a row on his bed. It was safer to store them here since he was spending most of his time in Dean’s room, sharing that bed. He bit down on the nail on his thumb, his arms wrapped around his torso. His foot was tapping nervously on the floor as he eyed his foes in front of him.

He can’t believe he actually agreed to this. No, that he actually _suggested_ it! He was officially, certifiably insane! There’s no way this could go well. Either he will be laughed out of the bunker, or he’s gonna screw something up and he will never live it down until the day he died.

But... he wanted to do it, as well. It would be interesting what this would result... If anything goes wrong he could abort it anytime... Dean was on board wholeheartedly. He spent half of last night convincing Sam to _‘Yes, fucking yes, I can’t wait to do this, Sammy baby!’_

How can he resist that?

So, here he was, glaring at the shopping bags, trying to intimidate them into submission.

Because this was insane!

And thrilling...

With a sigh of resignation, he stepped to his bed and emptied the bags onto the mattress. He tried to dismiss the memory of his shopping trip, but the girl at the cash register had been a sweetheart, helping him without judgement once she realized what he was planning. She helped him choose the proper articles, making him try them on promptly. She had been honest with him, bringing other articles in until they found the perfect ones and never pulling the punches. In this case, Sam would’ve kissed the ground she walked on in his gratitude.

His eyes slid onto the case resting on the nightstand. She had even given him tips on _that._

No more stalling! He might as well start this before Dean got back from the car wash.

He began unbuttoning his shirt.

* * *

 

Dean began whistling as he got out of the Impala, letting his eyes roam over her shiny black body appreciatively. He made sure not to leave any fingerprints on the sleek surface as he walked away and made his way out of the garage. He shed his jacket off, throwing it into his bedroom as he passed it by. The merry tune cut off when he realized Sam wasn’t in there.

With a shrug he went to the kitchen, his second guess for possible locations where Sam could be. It was on his way to his first guess.

The kitchen was empty.

Dean frowned as the silence of the bunker reached his ears. Where was his brother that his absence could generate such vacuum? Usually there would be some noise around, a book falling over on a shelf, a pipe creaking in the wall, or maybe the TV or some music playing softly...

This silence was eerie...

Yet filled with anticipation.

"Sammy?" he called out as he reached the map room. He looked around, turning towards the library...

And halted mid-step.

Jaw hanging open.

The figure in the library stepped forward and into the light.

"Professor Winchester?"

Dean blinked a few times, trying to decide if he was seeing things.

Because there’s no way badass hunter Sam Winchester was standing in front of him.

Wearing a freaking SKIRT!

The air stuck in his lungs exploded out in a choked gasp as Dean’s body reminded him of its existence. He was pretty sure he lost a lot of blood - and some brain cells.

"S... Sam...?" he wheezed out once he managed to get some oxygen.

Sam took another step closer, white teeth clamping down onto a cherry red lower lip, shining in the light with... lipgloss? Slanted hazel green eyes lowered, hiding behind long lashes, longer than usual. Their fox-like mischievous gaze was enhanced by a light redness on the cheeks, but Dean was sure it wasn’t just a blush Sam was fighting.

Dean’s eyes slid down his brother’s body, roaming over the white, long-sleeved blouse on the lean torso, a black tie laying over the buttons, loosened under a popped-open button. It was practically molded to the muscles and curves and Dean was pretty sure he could see Sam’s nipples through the thin material... just like a girl’s small breasts... without a bra...

The hem of the blouse ended way above Sam’s hips, the bones protruding through his tanned skin in that oh-so-delicious way Dean fell in love with. Under them started the skirt, leaving a wide strip of Sam’s stomach free, ready to be devoured by hungry lips... like Dean wanted right now...

The skirt was plaid and pleated and _short!_  Dean felt his poor brain fry at the sight of those long legs, firm, strong thighs tinted bronze under the lamplight. They looked bare, not a hair on them as far as he could see. Did Sam... _**shave?!**_

The kid was even wearing knee-high stockings and buckled shoes school girls wear!

"Is everything okay, professor?"

Dean startled at Sam’s voice. It was soft and shy, yet deep and so fucking _seductive!_  Dean just wanted to lay Sam onto the table and take him then and there! His eyes flew back to Sam’s eyes, searching for answers and trying to get his brain back online.

Those hazel-greens burned with a fire Dean had only seen a portion of so far.

And a lock of those chestnut-brown tresses had fallen into them.

Wait, where was the rest?

But a second later and a couple inches higher he found the answer. He let out another choked gasp, his jeans growing even tighter from the realization.

Tied into a ponytail!

Dean might need a change of shorts now.

"I can come back later" Sam spoke when he failed to get a response from Dean. The older brother watched as the younger man’s features slid into a disappointed pout, but then movement from lower drew his attention away. Sam’s left knee was bent and drawn in, his foot twisting on the floor, just like the schoolgirls in animes or porn movies do and Dean was definitely in need of a new pair of boxers now.

"No!" he practically screamed. He wanted to hit himself when Sam genuinely startled at his outburst, but _goddamn!_  Give a guy a break! He wasn’t exactly expecting... _**this!**_

"I-I’m sorry, Sam" Dean spoke quickly before things took a wrong turn. "You just surprised me. What are you doing here?" He walked slowly closer, unable to keep his eyes on one place for long. This... This was something he needed to sear into his memory forever.

"Don’t you remember?" Sam’s soft voice had a hint of hurt in it. When Dean looked up into his eyes, though, it was coy and full of fire once again. "You promised extra lessons for Biology. To help me improve my grades."

"Right" Dean nodded, feeling his mind settle into the space of make-believe. They hadn’t planned the scene out in advance, he basically just said _‘Fuck, yes!’_  to the first thing Sam suggested. It doesn’t matter, though: this was more fun... with more surprises for both of them. "Can’t have you besmirching those straight As with a B, can we?"

Sam smiled shyly at him, tilting his head in that flirty way that, as far as Dean knew, only girls could pull off. And his little brother, apparently. A slender finger lifted from behind Sam’s back and caressed Dean’s chest where his shirt buttons were lined up, slow and deliberate. In turn, Dean reached up and let the tip of his index finger stroke down Sam’s jawline, barely there and teasing. He felt Sam shiver even with the few inches of space between them.

Suddenly Sam took a step back then turned around. Dean could only stand and watch his brother’s hips swaying invitingly as Sam walked up to the table behind him. The pleats of his skirt were brushing the top of his thighs, only once revealing the curve of a firm cheek as they moved. Dean wanted to sink his teeth into it as the material tickled the bridge of his nose...

Sam then lowered himself onto the desktop and Dean thought the Earth spun a fast 180 under his feet as those long, long, _long_ legs crossed so, _so_ elegantly. Where has Dean been all this time that he didn’t know his brother was capable of... _this?!_

"When do we start, professor?"

The way Sam was leaning back onto his hands made his chest curve forward and Dean saw the younger man’s nipples practically tearing holes into the blouse. And did he even mention how much curvier Sam looked like this? A woman would turn dark green with jealousy!

"Right now" he finally answered, walking up to his little brother, who gazed at him through his lashes. The kid was a pro! Dean felt proud and a bit jealous at the same time. Where did he learn to seduce this efficiently? "This is why you’re here, right?"

"Yes, sir..."

And that tiny word shouldn’t have that much effect on him.

"So" Dean spoke, feeling stable enough to pick up his role. "Where are we in your class exactly?"

"I think" Sam pursed his lips so prettily, Dean wanted to kiss him and bite them, to lick the lipgloss and lipstick off of them... "Male anatomy."

Dean choked on his oxygen a third time. He was gonna asphyxiate if he can’t get a hold of himself. This isn’t even a silver platter, it’s a silver plated honeymoon suite at this point. Once he gathered his brain up from the tiled floor, he chuckled and shook his head.

_‘One more cheeky word and I’m gonna spank your pretty, curved hind, lil’ bro’_ he thought, but kept it to himself.

"Well, then" he spoke, leaning his hand onto the desk, bringing his face close to Sam’s. "Let’s get started."

His free hand settled onto Sam’s thigh and slowly inched up towards the skirt. Sam straightened up to free his own hands and one grabbed the hem of his skirt and pulled it - down.

Dean tilted his head a bit confused, but when he looked up, he found Sam watching him with wide eyes, his lower lip ensnared by his teeth once more. The hazel-green was flashing with flames and hope and love and uncertainty - the last one Dean recognized as part of the role.

He let his nails dig a tiny bit into Sam’s bare thigh and he pulled them down, applying enough pressure to tickle but not enough to hurt. Sam shivered with a loud inhale through his nose and Dean used the slight distraction to evade the obstacle. His fingers slid under the skirt, traveling towards the back.

"Sir?" Sam whispered, his eyes now losing their slanted shape as they widened even more.

"It’s okay, sweetheart" Dean replied breathily. "Part of the lesson, I promise."

With that, he loosened the reins on his instincts and carefully leaned in.

The kiss was soft and probing at first. Sam’s hands moved, one resting on Dean’s shoulder while the other, the one keeping his skirt still, slid up the older man’s chest. A tiny whimper escaped Sam’s lips when Dean leaned forward some more, pressing their mouths together with more force. Dean took the opportunity and opened his own mouth, capturing Sam’s lower lip and sucking it in. Sam gasped in surprise, as his role demanded it, which in turn opened the way in.

Dean lifted his hand and cradled Sam’s neck, holding him in place to deepen the kiss. Sam’s hand on his chest settled onto the back of his head. Dean could feel his brother’s legs uncrossing and Sam slid forward, pressing their chests together. The warmth of Sam’s body sent Dean’s senses into overdrive and his hips made a small thrust forward, wishing for release and wonderful, heavenly heat.

That snapped him out of the trance those thin, delicious lips usually put him into and he pulled away. He smirked when Sam tried to follow him, but his own gasp for air reminded him that he had lungs for a reason.

Damn shame, though... To give those lips up for something as trivial as oxygen...

"Now" Dean said, stepping back and pulling a chair out. As he slid his hand off Sam’s thigh, he made sure to shift the skirt back into place to cover Sam’s groin sufficiently. Sam seemed to freeze in shock at the sudden change of mood. He looked so damn beautiful with wide eyes and flushed lips, trying to catch up with the scene. "The male anatomy is very simple."

He sat into the chair he placed in front of Sam and looked into his eyes, raising his eyebrow with a challenge. Sam stared back a moment, obviously confused, but soon his face cleared of the fog. He slid off the table and sashayed over to Dean, his face arranged into perfect curiosity.

At that moment, one of the leashes in Dean’s mind snapped in half: he leaned forward, pulled Sam closer and descended onto that strip of skin teasing him all this time. He dragged his tongue over it horizontally, stopping briefly in the center to part the blouse and fondle the bellybutton. Once he reached the other side of Sam’s waist, he sucked a dark, almost black hickey onto Sam’s skin, right on top of his protruding hipbone. Sam must have shaved or waxed, because his happy trail to his groin was gone, leaving only smooth skin behind.

Sam’s back curved in, pressing his stomach into Dean’s face. The older brother could just picture Sam’s head thrown back, his mouth parted in pleasure, his neck stretched out for the world to see, his Adam’s apple bobbing with the swallowed moan. The slender fingers gripped the back of Dean’s head, curling around the short, blonde tresses, sending pinpricks through Dean’s scalp.

Satisfied now, Dean pulled back, brushing his thumb over the bruise. He looked up at Sam, who returned his gaze, eyes darkened by lust, pupils dilated already.

"Sit" Dean ordered, leaning back. His voice was deeper now. Sam turned to the side to lower himself onto one thigh, but Dean grabbed his hips. "No" he said, pulling Sam forward. _"Sit."_

Sam hesitated only for a moment, before he straddled his brother. The hem of the skirt practically burned Dean’s legs through his jeans as it flared over them. Dean let his hands slide up from Sam’s hips to his back, while Sam embraced his shoulders loosely. Dean leaned in and took a whiff of his brother’s scent.

It was mixed with a sweet aroma... Like perfume...

"Oh, baby" he breathed into the warm skin. "You smell fuckin’ amazin’..."

"S-Sir?" Sam’s tiny stutter fit his role, the uncertain schoolgirl, but Dean could hear the hitch of arousal in that deep tone.

"Tell me about the male reproductive organs, Sam" Dean said, his voice now husky with anticipation. Sam leaned back, staring down at him hesitantly and Dean wanted to kiss the kid’s brains out, he looked so _perfect!_

"A man has... um..." Sam began innocently, his cheeks reddening under the rouge. "He has a p-penis and... two t... testicles, right?"

Dean’s might have just exploded then and there.

"Correct" he managed. His hands slid off of Sam’s back and settled on the younger man’s ass, cupping and massaging them tenderly. Sam’s eyes slid shut momentarily, his lips tightening as he fought an urge flaring up inside him. Dean knew exactly what it was: whenever he paid attention to the kid’s ass like this, Sam would always suck on his throat. But he couldn’t do that without breaking the scene.

It was a surprisingly arousing sight, him restraining himself...

"The testicles produce the..." Sam continued after a shaky breath, swallowing erratically. His voice also grew huskier, but it managed to stay soft and innocent. "The semen... which comes out through the p-penis..."

"And what do we call that process?" Dean asked, already forming the next step in his head.

"Um..." Sam’s face grew even redder if that was possible and he averted his eyes shyly. Out popped the teeth, capturing the lower lip again. Dean loved that habit of his brother’s so much, but he was sure this will make him get a Pavlovian reaction every time he’ll catch a glimpse of it. Which would be awkward... "E-Ejacla... Um... Ejaculation, right?"

"Correct again" Dean praised his brother with a smirk. Sam even succeeded to sneak in a flub. Impressive and adorable... "Why don’t we do a little..." he paused for dramatic effect "demonstration?"

Sam’s beautiful eyes widened and the corners of his lips twitched as he realized what his big brother offered. Dean enjoyed catching the kid off guard maybe a _little_ too much.

"R-Right now, sir?"

"Of course" Dean nodded, narrowing his eyes. "You’re here for a lesson, aren’t you?" Sam’s eyes slid down deliberately, landing on Dean’s zipper. A second later, he began sliding backwards to stand up, but Dean tightened his grip on Sam’s ass, stopping the movement. Sam’s eyes shut tight momentarily before he looked back up at Dean. "Stay" the older man barked out, just shy of a general’s order. There’s no way he’ll let this minx slip out of his grasp now.

At last, Sam’s hands slid off Dean’s shoulders and onto the zipper. His fingers trembled as they slowly undid the button. The strain on the front of the jeans immediately slid the zipper down somewhat. Sam swallowed audibly as he reached out and helped its journey to be completed.

Then one hand disappeared inside the jeans.

And the boxers.

Dean was late to catch the start of a pleased moan, but managed to suppress the rest of it. He tensed as warmth embraced his already raging erection, battling the reflexes of his body.

"Th-This is the p-penis" Sam murmured distractedly. The kid must be eager for action, as well, it seemed, but Dean would lie if he said he didn’t enjoy the foreplay. The fingers let him go and slipped further in, cupping Dean’s balls one by one. "And these are the t-testicles."

"Yeah, that’s right" Dean breathed out, his hold on Sam tightening with every brush of Sam’s skin on his. He gasped in some air when his lungs started burning.

"Should I...?" Sam began, looking at him imploringly. Dean, however, ignored his question as he yanked his jeans and boxers down enough to free himself without dislodging the warm figure from his lap.

"So" he forced himself to return to his role, "what can induce an ejaculation?"

Sam’s hand lifted away from Dean, almost tearing a growl of protest from him.

"Several things" he replied. "Touch, for example..." His index finger slowly brushed the underside of Dean’s erection, which had the man tensing up to stop his hips thrusting up. "Or... maybe oral stim... stimulation..." The finger returned to the base and pressed onto the thick vein before sliding up on the underside again. "Would you like me... to demonstrate?"

"No" Dean shook his head quickly. There’s no way he’ll waist this for that. "What else?"

"The usual is... um..." Sam glanced up at Dean through his lashes and Dean will snap right now if his bastard little brother will tease him one more time- "Sexual intercourse, right?"

"Very good, Sam" Dean replied, pulling Sam in now, ready to move this along. The hem of the skirt tickled his erection, almost making him fly off the chair. "Let’s study this method a bit more, shall we?"

"If you say so, sir" Sam nodded, his hands returning to Dean’s shoulders, massaging the back of his neck and stroking his hair. Dean eased his hold on Sam’s ass, acknowledging - barely - that there will be bruises there tomorrow. His fingers slid further under the skirt until they reached fabric...

_Silk!_

Dean recoiled in surprise, staring at Sam. The younger man’s eyes flashed mischievously and he ground into Dean’s palms in invitation.

Sam was wearing panties.

Dean was in love with him.

He explored further and his heart doubled like the Grinch’s at Christmas.

_Silk, **lacy**_ panties!

As his index finger snuck under the fabric, searching for the warmth he was longing for, he found wetness.

Dean leaned up and rewarded Sam with a deep, sensual kiss for being a boy - or in this case, girl - scout. Sam leaned in eagerly, his tongue caressing Dean’s slowly, but then his body resonated with a deep moan: Dean slipped a finger through his brother’s tender entrance.

"Sir" Sam breathed out into Dean’s mouth, whining softly as Dean’s finger sank into him fully. "Please..."

"Good girl" Dean replied the same way, pushing Sam’s hips into his own and meeting him halfway. "Such a good, pretty girl, Sammy..."

Sam’s lips clumsily closed over Dean’s upper lip as another finger penetrated him, still probing and checking.

"Hold me, sweetheart" Dean whispered. He grabbed one of Sam’s hands and led it to his erection. "Take me in."

"Where, sir?" Sam asked, his fingers gently embracing the throbbing member. They hesitantly slipped up then down, drawing a loud moan out of the older man. Dean lifted Sam slightly and scooted down a little. Sam let him go and reached back to grasp him again.

"Feel that, Sammy?" Dean asked, letting his fingers slip into the lubed warmth. Sam moaned before nodding erratically. "That’s where I want to be."

"O-Okay..." Sam guided the tip of Dean’s erection to his entrance. Once the fingers slipped out of him, he lifted his eyes onto his big brother’s, locking their gazes, sending their love to each other without words.

Then Sam began sinking down.

The cherry-red, lipstick-smudged lips parted with a choked moan. Sam’s fingers fisted Dean’s shirt collar tightly. Dean leaned forward and buried his face into the crook of Sam’s neck, sucking on the thrumming pulse point and the collarbone poking out from under the blouse. Sam’s head tilted forward, forehead bumping Dean’s shoulder. As he sank lower and lower, Dean bit down on his brother’s shoulder, straining to hold himself back. He won’t embarrass himself by coming too early, dammit!

When Sam’s weight settled back into Dean’s lap, the younger man let out a long, whining sigh. Dean caressed Sam’s ass lovingly, his fingertips brushing at the point where he was buried into his brother.

"Perfect" he whispered into Sam’s neck, almost purring with ecstasy. "Such a perfect girl..."

Sam shivered with a soft hiss, his muscles tightening around Dean, which in turn tore a gasping moan out of the older man.

"Now w-what, s-sir?" Sam asked shakily, his own strain obvious in his voice.

"How do you feel, sweetheart?" Dean asked after he gulped, lifting his head up to check on his brother.

"Good..." Sam replied in a breathy tone. "F-Full..."

"Wonderful" Dean nodded. "Then we can start." He cupped Sam’s downturned head and pulled him into a kiss. At the same time, he gripped the younger man’s waist and began slowly lifting him up. Sam fumbled for support as friction took over his senses. He fisted Dean’s hair tightly, the man’s collar still imprisoned by his other hand. As he was lifted, the brothers’ lips were separated and Sam gasped.

"No... Not yet..."

"Shh, Sammy" Dean soothed, amazed by his ability to speak despite the sensations keeping him trapped. "Trust me..."

With that, as only the tip of his erection stayed inside Sam, he started lowering the younger man back into his lap, in an excruciatingly slow pace.

Sam moaned out loud, audibly dissatisfied.

"Your turn, baby" Dean whispered, his mouth brushing at Sam’s as he spoke. "You know what to do now..."

Sam slotted his mouth over his brother’s, opening it up with his tongue before invading. In the meantime, his hips lifted once more, without any guidance from Dean.

Then slammed back down.

They both groaned into each other’s mouths and Sam ground his hips against Dean’s. A small jolt and a gasp indicated that the tip of Dean’s erection rubbed at the sweetest spot inside him.

"There" Dean noted. "That’s where your pleasure is. Go for it, baby..."

This time, when Sam slammed himself back down, his hips moved in an angle.

And Sam let out a cry of triumphant ecstasy.

"Good..." he whined out, moaning when he ground his hips again. "So good..."

"Let me see you, sweetheart..." Dean breathed and leaned back in his seat. He reached down and lifted the skirt, revealing the bright pink silk panties.

And Sam’s rock hard erection that slipped out of it.

Dean wrapped his fingers around his brother’s member and began slowly stroking it up and down. Sam whined out loud at the new sensation assaulting him and his steady rise faltered momentarily. Soon, however, he slammed back down, and as he ground his hips, he thrust into Dean’s hand. Dean let his thumb rub over the slit at the tip, the foreskin already pulled back to reveal that bundle of nerves. Sam cried out in pleasure at that, his head snapping back as his back arched. Dean could feel the slippery precome drip out and he used that to smooth the path of his fingers on Sam.

"Squeeze me as you lift up" he ordered, demonstrating his wish on Sam’s erection. Sam sobbed out another moan but when he moved upwards, his muscles tightened around Dean. Their moans of pleasure ricocheted off the walls of the empty bunker, flowing into the corridors.

"Sammy..." Dean groaned and his free hand flew up to his brother’s head. He yanked Sam down into a kiss, the two battling each other fiercely even as they kept their established motions. Air and moans and tremors and pleasure was exchanged between their lips, unending and wonderful and unbelievable...

Their pace gradually picked up and it tore them apart, but Dean instantly latched onto Sam’s neck while Sam gasped out rhythmic breathy moans above him. Dean’s hand moved faster on Sam’s erection, as well, rubbing the tip with his thumb over and over as much as he could, since he starved for the soft mewls and loud groans that produced. The chair started creaking at their fluctuating weights, squeaking loudly in protest when Sam bounced hard. Dean’s other hand now had Sam’s blouse in its grasp.

"I’m... I’m c-close..." Sam keened aloud, not letting up the pace. Dean squeezed his brother in answer.

"Come for me, Sammy..." he breathed into the dampening skin.

Sam’s body grew rigid and the younger man let out a shout. His inner muscles tightened around Dean, who in turn let himself finally tip over the edge. His own yell, his brother’s name soaring with it, was muffled by Sam’s shoulder.

As their bodies unwound, Sam collapsed into Dean’s chest, his head landing on the older man’s shoulder. The echoes of their voices was slowly overtaken by frantic, breathless panting as they waited for the adrenaline to settle. Dean wrapped both his arms around Sam, rubbing his back erratically, weak and spent. Although, he still shuddered in pleasure as Sam’s breaths breezed over his throat, cooling down the sweat gathered on his skin.

A couple minutes later, steadier and relaxed, Dean squeezed Sam’s body.

"District?" he offered, his voice cracking from exertion but at least he was functioning now. Sam let out a sigh then nodded.

"District..." his soft voice was content, which warmed Dean’s heart.

"Holy shit" the older brother exclaimed. "You’re... amazing."

"Thanks" Sam snorted. His arms slid tighter around Dean’s shoulders.

"Where the hell did you learn all this?" Dean asked curiously. "Is there something about Stanford you’re not telling me?"

"No" Sam was now laughing. "I... I’ve never done this before."

"Then you’re a fucking natural" Dean said, shaking his head in disbelief. "Who knew uptight, virginal Sammy Winchester can be such a slut?"

"Shut up" Sam weakly swatted at Dean before lifting his head to glare at his brother. His lips, however, were twitching upwards. "I’m not a natural and this felt a little awkward. It’s not how I behave, but... I just love you that much."

"You’re such a chick, Sammy" Dean replied, but he smiled lovingly at his brother. Sam rolled his eyes but kissed him gently, caressing Dean’s stubbly cheek with the back of his fingers.

"We should clean up" the younger Winchester suggested during the split second their lips parted. Dean pressed into the second kiss then leaned back.

"Shower?" he suggested with a smirk.

"Absolutely" Sam smiled back, this time his expression sly and willing. They carefully separated from each other and Sam adjusted his clothes while Dean shoved the chair under the table.

"You know" Dean spoke, crossing his arms and sizing up his brother when Sam looked at him curiously, "you’re fucking sexy in this get-up."

Sam’s eyebrows slid up his forehead, but Dean let his eyes roam over the curve of the younger man’s torso, the black hickey on the protruding hipbone and the long, _long, **fucking long**_  legs.

"You... think so?" Sam asked hesitantly, his cheeks, as usual, flushing from embarrassment.

"It’s not a good enough word for you, but it’ll have to do" Dean shrugged. "You’re porn on legs. A high-production one, not those cheap shits in cockroach motels."

"From you, I’ll take that as a compliment" Sam replied, his voice shaking with suppressed laughter, but the glitter in his eyes betrayed his appreciation and gratitude. Dean shook his head with a huff of laughter then walked up to his brother.

"After you" he waved his hand towards the corridor leading to their bedroom.

"You just wanna stare at my ass, don’t you?" Sam accused light-heartedly, placing one hand on his hip in mock annoyance.

"You know me so well."

Sam huffed at the reply, but before he walked off, he sidled up to Dean, looking at him with a flirty smile.

"So, do I pass, professor?" he teased, stroking Dean’s shirt seductively. Dean pulled his brother close and into a kiss before replying:

"Straight A pluses until you graduate, babe. Guaranteed."

_TBC_

**Notes for the Chapter:**

> Hope you liked it! This is my first real smut and it might be light considering... It's enough to make me blush during writing. :/
> 
> Later scenes will be more separated from the story's reality and I'll make it more noticeable.
> 
> Hope to see you soon!


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